10 of the best women dressed as men

Surface male … Katy Stephens as Rosalind (as Ganymede) in a 2009 RSC version of As You Like It.

Orlando Furioso by Ariosto

Bradamante covers herself with armour and fights as a manly knight. “He” is befriended by the Saracen warrior Ruggiero, who realises his luck is in when his new comrade takes off her helmet and shakes out her long tresses. Ruggiero is instantly love-struck.

As You Like It by William Shakespeare

The bard loved to give us a bit of cross-dressing (Portia, Imogen, Viola, Julia …), but with Rosalind he outdid himself. In As You Like It he has a boy actor playing a woman who dresses up as a man who pretends to be a girl (in order to help Orlando with his wooing). Talk about fluid ideas of gender …

Don Quixote by Miguel de Cervantes

Out in the wilderness, Don Quixote’s friends are looking for the deluded knight. They meet Dorothea, a young woman wearing male clothing. She tells her tragic story – she has been seduced then discarded by a rich man’s son and has adopted this disguise in order to flee.

The Roaring Girl by Thomas Middleton and Thomas Dekker

The thief Moll Cutpurse dresses in a man’s clothes but arouses the interest of many male admirers. When her would-be lover Laxton arranges a rendezvous, she arrives in disguise and fights him with a rapier. “Venus … passes through the play in doublet and breeches, a brave disguise and a safe one if the statute untie not her codpiece point.”

The Country Wife by William Wycherley

Margery Pinchwife’s cruel husband is terrified of being cuckolded, so when he takes her out to the shops in London he dresses her as a young man. However, the rakish Horner is in on the trick and takes the opportunity to kiss and manhandle the “pretty” gentleman in front of the tormented Pinchwife.

The Rover by Aphra Behn

Our heroine, Hellena, disguises herself as a young gent so she can prevent the man she loves, Willmore, succumbing to Angelica, a famous courtesan. In her male guise she tells Angelica a story of Willmore’s affair with another woman, rousing her to fury and alienating her from the “roving” Willmore.

The Monk by Matthew Lewis

The dark, brooding monk Ambrosio – a pillar of rectitude – is attended by an admiring young novice, Rosario. “He seemed fearful of being recognised, and no one had ever seen his face. His head was continually muffled up in his Cowl.” No wonder – for one day in Ambrosio’s cell he reveals himself to be the beautiful Matilda, and effortlessly seduces the devout Ambrosio.

Lord of the Rings by JRR Tolkien

Éowyn desperately wants to avenge her father, killed by orcs. She disguises herself as the male warrior Dernhelm and fights alongside the Riders of Rohan in battle, even managing to kill the Lord of the Nazgûl – who has boasted that no man can ever defeat him and is nonplussed to discover that his opponent is, in fact, a woman.

Tipping the Velvet by Sarah Waters

Nan Astley, a simple girl from Whitstable, falls for male impersonator (or “masher”) Kitty Butler, whom she sees strutting her stuff on stage. Eventually she joins her in the act, and later walks the streets of London dressed as a man. When she is picked up by the wealthy widow Diana she cohabits with her in the guise of “Neville”.

Monstrous Regiment by Terry Pratchett

Searching for her brother, who is missing in action, Polly Perks cross-dresses in order to join the Borogravian army. She befriends another squaddie, Lofty Tewt, who confides that “he” too is a girl. Slowly the truth becomes apparent: everyone in the regiment is in fact a woman dressed as a man. Naturally, they triumph in battle. JM